218444-38-3Relevant academic research and scientific papers
Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus
Wu, Deyan,Mei, Hanbing,Tan, Ping,Lu, Weiqiang,Zhu, Jin,Wang, Wei,Huang, Jin,Li, Jian
, p. 4383 - 4387 (2015/06/22)
In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential.
Total synthesis of moracin C
McAllister, Graeme D.,Hartley, Richard C.,Dawson, Michael J.,Knaggs, Andrew R.
, p. 3453 - 3457 (2007/10/03)
Moracin C has been synthesised by the most efficient route to date (10 steps and 12% overall yield). The relatively unexplored acid-induced, intramolecular migration of an acyl group from an ortho phenolic hydroxy to a benzylic hydroxy is used to synthesise o-hydroxybenzylphosphonium salts containing ester groups. The phosphonium salts are coupled with 3,5-dimethoxybenzoic acid. Intramolecular Wittig reaction then gives 2-arylbenzo[b]furans, bearing the key 1′,3′,5′ substitution pattern on the aryl ring. This discovery provides a concise route to polyphenolic benzo[b]furans that we expect to be of general utility.
